Viability of a covalent chiral auxiliary method to induce asymmetric induction in solid-state photoreactions explored

Arunkumar Natarajan; Joel T. Mague; V. Ramamurthy

doi:10.1021/cg0501175

Viability of a covalent chiral auxiliary method to induce asymmetric induction in solid-state photoreactions explored

Arunkumar Natarajan, Joel T. Mague, V. Ramamurthy

Chemistry

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

The effectiveness of covalent chiral auxiliaries in inducing stereoselectivity during the Yang type II photocyclization reaction was examined using the benzonorbornene phenyl ketone (2) and α-adamantylacetophenone (7) systems. The outstanding ability of covalent chiral auxiliaries in generating high asymmetric induction in the photoproducts has been established in 7 of the 10 investigated examples. Three examples in which molecules crystallize with equal amounts of conformational isomers in the asymmetric unit, despite the covalently linked chiral auxiliary, highlight the limits of the use of the covalent chiral auxiliary approach for asymmetric induction in the solid state.

Original language	English (US)
Pages (from-to)	2348-2355
Number of pages	8
Journal	Crystal Growth and Design
Volume	5
Issue number	6
DOIs	https://doi.org/10.1021/cg0501175
State	Published - Nov 1 2005

ASJC Scopus subject areas

Chemistry(all)
Materials Science(all)
Condensed Matter Physics

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abstract = "The effectiveness of covalent chiral auxiliaries in inducing stereoselectivity during the Yang type II photocyclization reaction was examined using the benzonorbornene phenyl ketone (2) and α-adamantylacetophenone (7) systems. The outstanding ability of covalent chiral auxiliaries in generating high asymmetric induction in the photoproducts has been established in 7 of the 10 investigated examples. Three examples in which molecules crystallize with equal amounts of conformational isomers in the asymmetric unit, despite the covalently linked chiral auxiliary, highlight the limits of the use of the covalent chiral auxiliary approach for asymmetric induction in the solid state.",

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N2 - The effectiveness of covalent chiral auxiliaries in inducing stereoselectivity during the Yang type II photocyclization reaction was examined using the benzonorbornene phenyl ketone (2) and α-adamantylacetophenone (7) systems. The outstanding ability of covalent chiral auxiliaries in generating high asymmetric induction in the photoproducts has been established in 7 of the 10 investigated examples. Three examples in which molecules crystallize with equal amounts of conformational isomers in the asymmetric unit, despite the covalently linked chiral auxiliary, highlight the limits of the use of the covalent chiral auxiliary approach for asymmetric induction in the solid state.

AB - The effectiveness of covalent chiral auxiliaries in inducing stereoselectivity during the Yang type II photocyclization reaction was examined using the benzonorbornene phenyl ketone (2) and α-adamantylacetophenone (7) systems. The outstanding ability of covalent chiral auxiliaries in generating high asymmetric induction in the photoproducts has been established in 7 of the 10 investigated examples. Three examples in which molecules crystallize with equal amounts of conformational isomers in the asymmetric unit, despite the covalently linked chiral auxiliary, highlight the limits of the use of the covalent chiral auxiliary approach for asymmetric induction in the solid state.

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Viability of a covalent chiral auxiliary method to induce asymmetric induction in solid-state photoreactions explored

Abstract

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